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Sir Andrew Aguecheek first appears in the third scene of Act I, as the so-called friend of Sir Toby Belch. Sir Andrew is a guest at the home of Sir Toby's niece Lady Olivia, where Sir Toby, a drunkard and glutton, resides. Although we are not made aware of Sir Andrew's family or connections, it is said that his annual income is 3,000 ducats,[1] a significant amount and roughly equal to that of a skilled craftsman of the period,[2] leading us to assume that he is a gentleman of some leisure. Ineptly, Sir Andrew attempts to court Olivia, and her rejection of him, in favour of dashing Cesario, prompts Sir Andrew to challenge Cesario to a duel. His slow-witted nature allows Sir Toby perfect opportunity to take advantage of him, even openly admitting that by playing to Sir Andrew's generosity and gullibility, he has milked him for approximately two-thirds of his stated income.[3] Sir Andrew fancies himself a great dancer and swordsman,[4][5] and the scenes where he ineptly engages in these activities are points of physical comedy in the play.[6] Sir Andrew's age is not made clear, but it is assumed that he is a number of years younger than Sir Toby.[7]

Sir Andrew and Malvolio are probably the only characters whose situation at the end of the play is not as favourable as in the beginning. Amongst three happy couples and a humiliated Malvolio in the final scene, Sir Andrew has already made his closing exit, following Sir Toby's open insults toward him.[8] Friendless and deep in debt, this ending echoes one of Sir Andrew's better known lines, from the third scene of the second act: "I was adored once too." The negative outcome for Sir Andrew, combined with his having been the subject of jokes and Sir Toby's greed, is a strain of melancholy in an otherwise comical play.

As one of the central supporting roles in Twelfth Night, Sir Andrew's character speaks a total of 152 lines and appears in seven of the eighteen scenes.[9]

Richard E. Grant played the part in Trevor Nunn's movie adaptation of Twelfth Night, dancing dreadfully in front of Mel Smith's Sir Toby, getting his sword caught in a branch of a tree and being kicked in the groin during his duel with "Cesario" (Imogen Stubbs). When Maria (Imelda Staunton) tricks Malvolio (Nigel Hawthorne) into wearing yellow stockings, she reveals to her fellow conspirators that "'tis a colour [my lady Olivia] abhors". They then turn to Sir Andrew who is wearing a yellow waistcoat, tie and stockings. Like the others, however, he is allowed some dignity by kissing the hand of Olivia (Helena Bonham Carter) before leaving her estate, his head held high.